1,2-Dichloroethane → N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-[4-(1H-pyrazol-4-yl)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 1522501Notes

Reaction equation

HRID 1522501 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:23]=[N:24][NH:25][CH:26]=4)=[CH:18][CH:17]=3)[CH:11]=[C:12]([C:13]([OH:15])=O)[C:7]=2[CH:6]=[N:5]1)[CH3:3].[NH2:27][CH2:28][C:29]1[C:30](=[O:37])[NH:31][C:32]([CH3:36])=[CH:33][C:34]=1[CH3:35].CN1CCOCC1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CS(C)=O>[CH3:35][C:34]1[CH:33]=[C:32]([CH3:36])[NH:31][C:30](=[O:37])[C:29]=1[CH2:28][NH:27][C:13]([C:12]1[C:7]2[CH:6]=[N:5][N:4]([CH:2]([CH3:3])[CH3:1])[C:8]=2[N:9]=[C:10]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:26]=[N:25][NH:24][CH:23]=3)=[CH:18][CH:17]=2)[CH:11]=1)=[O:15]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 671241631-(1-Methylethyl)-6-[4-(1H-pyrazol-4-yl)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 56599207N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-[4-(1H-pyrazol-4-yl)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared in the same manner as described in example 109 using 1-(1-methylethyl)-6-[4-(1H-pyrazol-4-yl)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (20 mg, 0.058 mmol), DMSO(1 mL), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (16.29 mg, 0.086 mmol), N-methylmorpholine (0.025 mL, 0.230 mmol), 1-hydroxy-7-azabenzotriazole (15.67 mg, 0.115 mmol) and EDC (22.07 mg, 0.115 mmol). The final product was collected as 12 mg (43%). LCMS E-S (M+H)=482.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.56 (d, J=6.4 Hz, 6 H), 2.14 (s, 3 H), 2.24 (s, 3 H), 4.42 (d, J=4.8 Hz, 2 H) 5.27-5.47 (m, 1 H), 5.91 (s, 1 H), 7.79 (d, J=8.3 Hz, 2 H), 8.04 (br. s., 1 H), 8.15-8.21 (m, 1 H), 8.27 (d, J=8.3 Hz, 2 H), 8.35-8.42 (m, 1 H), 8.99 (t, J=4.8 Hz, 1 H), 11.58 (br. s., 3 H).

Workup

  1. customThe final product was collected as 12 mg (43%)

Sources & evidence

ORD record
ord-9f441bfd6e6e4e2c958e58a9cce2878e
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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